How to build a portfolio of small bets (without hating your life):
Remember that to thrive, you must first survive. The order matters.

Instead of trying to succeed, try not to fail. Make sure your self-employment arrangement becomes sustainable quickly by going for the low hanging fruit.
Low hanging fruit are opportunities that require very little cost, time, and effort — even if it means they're not the most enjoyable and have limited upside.

Try as many of these "small bets" as you can, and run them in parallel — no need to wait for a failure to do the next.
What you consider low hanging fruit depends a lot on your circumstances. Explore your strengths and opportunities, and try to imagine some quick wins you can pursue. Once survival stops being a pressing concern, you can go for more ambitious opportunities.
Keep all bets safe-to-fail, and ideally cannot-fail. Mix different types of bets to tame the uncertainty of each bet. As some start to work, eliminate those that are least enjoyable.

As soon as you can afford it, optimize for enjoyment. Otherwise, this arrangement won't last!

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More from @dvassallo

7 Apr
For #GumroadDay, my info products are 'Pay What You Want', $1 minimum. Today only.

- Everyone Can Build a Twitter Audience, $40
- The Good Parts of AWS, $25

These 2 products made $332,667 in sales so far. Go see what they look like!

👉 dvassallo.gumroad.com
An average of 1 sale every 12 seconds in the first hour. 301 sales in 60 minutes. Thank you! — 23 hours to go.
Almost 2,000 sales in the first 12 hours of #GumroadDay. Thank you!

12 hours left.
Read 4 tweets
8 Mar
Everyone wants to decouple time from money.

The problem? It's an extremely unpredictable way to make a living. For every successful creator, there are thousands who make nothing or almost nothing.

So, how do you make the unpredictable, predictable? Here's what I learned:
See, there are two very distinct worlds of how to make a living in our universe.

The first world is the one we're mostly familiar with, where you follow a predictable career path.
Say you want to make a living as a programmer, a doctor, a plumber, an English teacher, etc. If you do certain things (learn to code, get a specific degree, etc.) you can increase the odds of getting what you want to very close to 100%.
Read 32 tweets
18 Feb
Why I find @joinClubhouse interesting:
1. Unlike Twitter, I almost never open the Clubhouse app. Occasionally I get a notification that someone I follow is speaking, and I get the option to drop in. The push system adds random pleasant surprises to my life.
2. I hate parties. The crowds, the small talk, the dressing up, the inability to avoid certain people... ugh.

But I like the idea of parties: An almost free opportunity for chance encounters that could lead to many things.

Clubhouse is my party substitute without the downsides.
Read 6 tweets
18 Dec 20
Which's the most important skill you should learn if you want to work for yourself? ...
Selling.

I don't think you learn this by reading about it, but by becoming determined to figure out what motivates people to take out their wallet and pay for things.
I started by observing my own behavior when I came to make purchasing decisions. Whenever I found myself choosing to pay for something (or choosing not to), I would try to reflect on why I was making that decision.
Read 6 tweets
18 Nov 20
Some of my favorite books and my main takeaway:
Punished by Rewards — People hate being controlled with carrots & sticks, and only intrinsic motivation lasts.

Man's Search for Meaning — A good life is a story you're proud of.

4 Hour Work Week — Design your lifestyle based on your preferences, not on preferences of others.
Unconditional Parenting — Be on your child's side, unconditionally, all the time.

Blue Ocean Strategy — Find uncontested markets.

Alchemy — Rational is what works, not what makes sense.

Rework — Constraints are advantages in disguise.

Hell Yeah or No — Do almost nothing.
Read 4 tweets
31 Aug 20
How to be happy (without getting lucky):
Learn your true preferences. Knowing what you dislike tends to be more reliable than what you think you'll like.
Try new things, but always keep a realistic option to quit. If you're on the wrong train, every stop is the wrong stop.
Read 15 tweets

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